11 insiders reported 39 Form 4 transactions for Upland Software, Inc. (UPLD) over the past 18 months (most recent 2026-06-16). Recent activity: Nathaniel Sean (CEO and President) Sell 18,605 shares, Hill Michael Douglass (CFO, Treasurer & Secretary) Sell 8,931 shares, Doman Dan (Chief Operating & Product Ofcr) Sell 29,515 shares, Nathaniel Sean (CEO and President) Buy 500,000 shares, Doman Dan (Chief Operating & Product Ofcr) Sell 33,491 shares. Source: SEC Form 4.
| Date | Insider | Title | Type | Shares | Value |
|---|---|---|---|---|---|
| 2026-06-16 | Nathaniel Sean | CEO and President | Sell | 18,605 | $11,282 |
| 2026-06-16 | Hill Michael Douglass | CFO, Treasurer & Secretary | Sell | 8,931 | $5,416 |
| 2026-06-16 | Doman Dan | Chief Operating & Product Ofcr | Sell | 29,515 | $17,898 |
| 2026-06-08 | Nathaniel Sean | CEO and President | Buy | 500,000 | $0 |
| 2026-03-17 | Doman Dan | Chief Operating & Product Ofcr | Sell | 33,491 | $18,085 |
| 2026-03-17 | Hill Michael Douglass | CFO, Treasurer & Secretary | Sell | 8,931 | $4,823 |
| 2026-03-17 | MCDONALD JOHN T | CEO | Sell | 18,605 | $10,047 |
| 2026-03-03 | Doman Dan | Chief Operating & Product Ofcr | Buy | 100,000 | $0 |
| 2026-02-25 | Doman Dan | Chief Operating & Product Ofcr | Buy | 150,000 | $0 |
| 2026-02-25 | Hill Michael Douglass | CFO, Treasurer & Secretary | Buy | 70,000 | $0 |
| 2025-12-17 | Hill Michael Douglass | CFO, Treasurer & Secretary | Sell | 8,856 | $13,195 |
| 2025-12-17 | Doman Dan | Chief Operating & Product Ofcr | Sell | 24,595 | $36,647 |
| 2025-12-17 | MCDONALD JOHN T | CEO | Sell | 19,677 | $29,319 |
| 2025-10-29 | Walsh Teresa Miles | Director | Buy | 25,000 | $0 |
| 2025-10-29 | Mattox Timothy | Director | Buy | 25,000 | $0 |
| 2025-10-29 | COURTER STEPHEN E | Director | Buy | 25,000 | $0 |
| 2025-10-29 | MAY DAVID | Director | Buy | 25,000 | $0 |
| 2025-10-29 | Chung David H S | Director | Buy | 25,000 | $0 |
| 2025-09-17 | Doman Dan | Chief Operating & Product Ofcr | Sell | 26,236 | $65,065 |
| 2025-09-17 | Hill Michael Douglass | CFO, Treasurer & Secretary | Sell | 11,152 | $27,657 |
| 2025-09-17 | MCDONALD JOHN T | CEO | Sell | 22,956 | $56,931 |
| 2025-09-11 | MCDONALD JOHN T | CEO | Sell | 14,438 | $34,074 |
| 2025-07-01 | Cummings Karen | President and COO | Sell | 40,993 | $79,936 |
| 2025-06-17 | Hill Michael Douglass | CFO & Treasurer | Sell | 11,152 | $20,520 |
| 2025-06-17 | MCDONALD JOHN T | CEO | Sell | 22,957 | $42,241 |
Source: SEC Form 4 filings · as of 2026-06-16